537029-30-4

Basic information

• Product Name: 1H-Imidazo[4,5-b]pyridine, 6-bromo-2-(3-methylphenyl)-
• CAS NO: 537029-30-4
• Molecular Formula: C13H10BrN3
• Molecular Weight: 288.147
• Mol File: 537029-30-4.mol

Chemical Properties

• CAS DataBase Reference: 1H-Imidazo[4,5-b]pyridine, 6-bromo-2-(3-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazo[4,5-b]pyridine, 6-bromo-2-(3-methylphenyl)-(537029-30-4)
• EPA Substance Registry System: 1H-Imidazo[4,5-b]pyridine, 6-bromo-2-(3-methylphenyl)-(537029-30-4)

Safety Data

• Hazardous Substances Data: 537029-30-4(Hazardous Substances Data)

Upstream product

• 38875-53-5 5-bromo-pyridine-2,3-diamine 
• 620-23-5 m-tolyl aldehyde 

Relevant articles and documents

Synthesis of 2-phenyl-1H-imidazo[4,5-b]pyridine as type 2 diabetes inhibitors and molecular docking studies

A series of imidazo[4,5-b]pyridines (3–32) was synthesized and evaluated for their ability to inhibit Baker’s yeast α-glucosidase enzyme. The IC50 values for all compounds were in the range of 13.5–93.7 μM with compound 15, a 2,4-dihydroxy-substituted analog, displayed the most potent activity potential. Structure–activity relationship strongly suggested the presence of hydroxyl group at aromatic side chain as the main contributing factor towards the inhibitory potential. Findings also suggested that compounds having hydroxyl groups at ortho and para positions are able to inhibit α-glucosidase enzyme efficiently. This experimental observation was further supported by docking studies carried out on human intestinal maltase-glucoamylase enzyme (PDB ID: 3TOP). The –NH– group of imidazo-pyridine of compound 15 formed H-bond with Asp1526, while both hydroxyls of catechol formed H-bond with Asp1279. Imidazo-pyridine ring was well stabilized by π–π stacking with Phe1560, and other hydrophobic interactions involving side chain of Pro1159, Tyr1167, Asp1157, Met1421, Trp1369, Pro1318, and Lys1460. The catechol ring also forms several hydrophobic interactions with Phe1560, Trp1523, Trp1418, His1584, Try1251, Ile1218 and Trp1355.

BICYCLIC DERIVATIVE, PROCESS FOR PRODUCING THE SAME, AND USE

The present invention provides a heterocyclic compound having potent tyrosine kinase-inhibiting activity represented by formula: (wherein, R1b is a C6-10 aryl group which has substituent(s), and the like; Ta is a single bond, a C1-6 alkyl group, -CH2O-, and the like; X and Y are the same or different, and each is a nitrogen atom which may have substituent(s), and the like; the broken line is a single bond or a double bond; Za is a nitrogen atom or CH; W is a single bond, an oxygen atom, and the like; Q is a C6-10 aryl group which may have substituent(s) or an aromatic heterocyclic group which may have substituent(s)); or a salt thereof and a pharmaceutical composition comprising thereof.